SE462972B - Nya bornanderivat, deras framstaellning och terapeutiska kompositioner innehaallande dem - Google Patents
Nya bornanderivat, deras framstaellning och terapeutiska kompositioner innehaallande demInfo
- Publication number
- SE462972B SE462972B SE8501884A SE8501884A SE462972B SE 462972 B SE462972 B SE 462972B SE 8501884 A SE8501884 A SE 8501884A SE 8501884 A SE8501884 A SE 8501884A SE 462972 B SE462972 B SE 462972B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- product
- compounds
- water
- tottoli
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 8
- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims abstract 5
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims abstract 4
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims abstract 3
- 229910052727 yttrium Inorganic materials 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 3
- 150000003254 radicals Chemical group 0.000 claims 1
- 150000002243 furanoses Chemical class 0.000 abstract description 2
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000003215 pyranoses Chemical class 0.000 abstract 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 3
- 229910006124 SOCl2 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229960004150 aciclovir Drugs 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- SRBFZHDQGSBBOR-TXICZTDVSA-N beta-D-ribopyranose Chemical compound O[C@@H]1CO[C@@H](O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-TXICZTDVSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XNMVAVGXJZFTEH-BUYFANAVSA-N (1r,2s,4r)-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-carboxylic acid Chemical compound C1C[C@@]2(C)C(=O)[C@@H](C(O)=O)[C@@H]1C2(C)C XNMVAVGXJZFTEH-BUYFANAVSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- SRBFZHDQGSBBOR-ZRMNMSDTSA-N D-arabinopyranose Chemical compound O[C@@H]1COC(O)[C@@H](O)[C@@H]1O SRBFZHDQGSBBOR-ZRMNMSDTSA-N 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-AIHAYLRMSA-N alpha-D-ribopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-AIHAYLRMSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical compound C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- -1 phenyl-4,5,6,7-tetrahydro-7,8,8-trimethyl-4,7-methano-indazol-3-one Chemical compound 0.000 description 1
- 238000002962 plaque-reduction assay Methods 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04H—BUILDINGS OR LIKE STRUCTURES FOR PARTICULAR PURPOSES; SWIMMING OR SPLASH BATHS OR POOLS; MASTS; FENCING; TENTS OR CANOPIES, IN GENERAL
- E04H1/00—Buildings or groups of buildings for dwelling or office purposes; General layout, e.g. modular co-ordination or staggered storeys
- E04H1/12—Small buildings or other erections for limited occupation, erected in the open air or arranged in buildings, e.g. kiosks, waiting shelters for bus stops or for filling stations, roofs for railway platforms, watchmen's huts or dressing cubicles
- E04H1/1272—Exhibition stands
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B2/00—Friction-grip releasable fastenings
- F16B2/20—Clips, i.e. with gripping action effected solely by the inherent resistance to deformation of the material of the fastening
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Architecture (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Public Health (AREA)
- Structural Engineering (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Civil Engineering (AREA)
- Mechanical Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848410484A GB8410484D0 (en) | 1984-04-24 | 1984-04-24 | Antiviral and antibacterial compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8501884D0 SE8501884D0 (sv) | 1985-04-17 |
| SE8501884L SE8501884L (sv) | 1985-10-25 |
| SE462972B true SE462972B (sv) | 1990-09-24 |
Family
ID=10560013
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8501885A SE462973B (sv) | 1984-04-24 | 1985-04-17 | Nya pyranoderivat, deras framstaellning och terapeutiska kompositioner innehaallande dem |
| SE8501884A SE462972B (sv) | 1984-04-24 | 1985-04-17 | Nya bornanderivat, deras framstaellning och terapeutiska kompositioner innehaallande dem |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8501885A SE462973B (sv) | 1984-04-24 | 1985-04-17 | Nya pyranoderivat, deras framstaellning och terapeutiska kompositioner innehaallande dem |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US4720487A (pt) |
| JP (2) | JPS60233095A (pt) |
| AR (2) | AR241916A1 (pt) |
| AT (2) | AT388558B (pt) |
| BE (2) | BE902232A (pt) |
| CA (2) | CA1265129A (pt) |
| CH (2) | CH665837A5 (pt) |
| DE (2) | DE3514641A1 (pt) |
| DK (2) | DK160832C (pt) |
| DZ (1) | DZ772A1 (pt) |
| ES (2) | ES8606379A1 (pt) |
| FI (2) | FI78302C (pt) |
| FR (3) | FR2563224B1 (pt) |
| GB (3) | GB8410484D0 (pt) |
| HK (2) | HK18788A (pt) |
| IE (2) | IE58322B1 (pt) |
| IT (2) | IT1215265B (pt) |
| LU (2) | LU85864A1 (pt) |
| MA (2) | MA20415A1 (pt) |
| MY (1) | MY102313A (pt) |
| NL (2) | NL193109B (pt) |
| NO (2) | NO161121C (pt) |
| OA (2) | OA07999A (pt) |
| PT (2) | PT80325B (pt) |
| SE (2) | SE462973B (pt) |
| ZA (2) | ZA852367B (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7622492B2 (en) | 2005-08-31 | 2009-11-24 | Hoffmann-La Roche Inc. | Pyrazolones as inhibitors of 11β-hydroxysteroid dehydrogenase |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868361A (en) * | 1973-03-12 | 1975-02-25 | Richard L Tolman | s-Triazolo{8 2,3-A{9 {0 pryimidine nucleosides |
| DE3019322A1 (de) * | 1980-05-21 | 1981-12-03 | Merck Patent Gmbh, 6100 Darmstadt | Psychopharmakon sowie verwendung von adenosinderivaten |
-
1984
- 1984-04-24 GB GB848410484A patent/GB8410484D0/en active Pending
-
1985
- 1985-03-28 ZA ZA852367A patent/ZA852367B/xx unknown
- 1985-03-28 ZA ZA852366A patent/ZA852366B/xx unknown
- 1985-04-01 US US06/718,065 patent/US4720487A/en not_active Expired - Fee Related
- 1985-04-01 US US06/718,064 patent/US4704454A/en not_active Expired - Fee Related
- 1985-04-10 AR AR85300028A patent/AR241916A1/es active
- 1985-04-10 AR AR85300029A patent/AR241917A1/es active
- 1985-04-17 SE SE8501885A patent/SE462973B/sv not_active IP Right Cessation
- 1985-04-17 SE SE8501884A patent/SE462972B/sv not_active IP Right Cessation
- 1985-04-18 CH CH1665/85A patent/CH665837A5/fr not_active IP Right Cessation
- 1985-04-18 BE BE0/214872A patent/BE902232A/fr not_active IP Right Cessation
- 1985-04-18 CH CH1666/85A patent/CH664572A5/fr not_active IP Right Cessation
- 1985-04-18 BE BE0/214871A patent/BE902231A/fr not_active IP Right Cessation
- 1985-04-19 MA MA20639A patent/MA20415A1/fr unknown
- 1985-04-19 MA MA20638A patent/MA20414A1/fr unknown
- 1985-04-22 PT PT80325A patent/PT80325B/pt not_active IP Right Cessation
- 1985-04-22 PT PT80324A patent/PT80324B/pt not_active IP Right Cessation
- 1985-04-22 FI FI851577A patent/FI78302C/fi not_active IP Right Cessation
- 1985-04-22 IT IT8520439A patent/IT1215265B/it active
- 1985-04-22 IT IT20440/85A patent/IT1201415B/it active
- 1985-04-22 FI FI851576A patent/FI78301C/fi not_active IP Right Cessation
- 1985-04-22 LU LU85864A patent/LU85864A1/fr unknown
- 1985-04-22 LU LU85865A patent/LU85865A1/fr unknown
- 1985-04-23 NO NO851619A patent/NO161121C/no unknown
- 1985-04-23 NL NL8501170A patent/NL193109B/xx not_active Application Discontinuation
- 1985-04-23 DE DE19853514641 patent/DE3514641A1/de active Granted
- 1985-04-23 GB GB08510329A patent/GB2158436B/en not_active Expired
- 1985-04-23 ES ES542485A patent/ES8606379A1/es not_active Expired
- 1985-04-23 CA CA000479845A patent/CA1265129A/en not_active Expired - Fee Related
- 1985-04-23 ES ES542486A patent/ES8606380A1/es not_active Expired
- 1985-04-23 NL NL8501171A patent/NL193067C/nl not_active IP Right Cessation
- 1985-04-23 CA CA000479844A patent/CA1241649A/en not_active Expired
- 1985-04-23 IE IE102985A patent/IE58322B1/en not_active IP Right Cessation
- 1985-04-23 GB GB08510328A patent/GB2157690B/en not_active Expired
- 1985-04-23 DK DK181285A patent/DK160832C/da not_active IP Right Cessation
- 1985-04-23 DE DE19853514637 patent/DE3514637A1/de active Granted
- 1985-04-23 IE IE103085A patent/IE58323B1/en not_active IP Right Cessation
- 1985-04-23 NO NO851620A patent/NO161122C/no unknown
- 1985-04-23 DK DK181385A patent/DK160833C/da not_active IP Right Cessation
- 1985-04-23 DZ DZ850084A patent/DZ772A1/fr active
- 1985-04-24 FR FR8506207A patent/FR2563224B1/fr not_active Expired
- 1985-04-24 OA OA58576A patent/OA07999A/xx unknown
- 1985-04-24 JP JP60086616A patent/JPS60233095A/ja active Granted
- 1985-04-24 OA OA58577A patent/OA08000A/xx unknown
- 1985-04-24 AT AT0122685A patent/AT388558B/de not_active IP Right Cessation
- 1985-04-24 FR FR8506204A patent/FR2563106B1/fr not_active Expired
- 1985-04-24 JP JP60086617A patent/JPS60233096A/ja active Granted
- 1985-04-24 FR FR8506206A patent/FR2563107B1/fr not_active Expired
- 1985-04-24 AT AT0122585A patent/AT388557B/de not_active IP Right Cessation
-
1988
- 1988-01-26 MY MYPI88000060A patent/MY102313A/en unknown
- 1988-03-10 HK HK187/88A patent/HK18788A/xx not_active IP Right Cessation
-
1989
- 1989-02-02 HK HK102/89A patent/HK10289A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0001981B1 (de) | Neue 9-(Omega-heteroarylamino-alkylamino)-erythromycine, ihre Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| EP0316704A2 (de) | Fluorcytidinderivate, deren Herstellung und Arzneimittel, die diese Derivate enthalten | |
| US4194045A (en) | 1-(3,3-Diaryl-3-oxadiazolalkyl)-4-phenyl-4-piperidinomethanols and related compounds | |
| US3936439A (en) | 2,6-Diaminonebularine derivatives | |
| EP0255894B1 (de) | Pyrimidinderivate, deren Herstellung und Arzneimittel, die diese Derivate enthalten | |
| US3651045A (en) | 9-(beta-d-arabinofuranosyl)adenine esters and methods for their production | |
| EP0314011A2 (de) | Purinderivate | |
| EP0292023A2 (de) | Pyrimidinderivate | |
| EP0058697A1 (en) | Novel rutin nona- and deca(h-)sulfate salts, methods of preparing novel salts, and use of novel salts as complement inhibitors | |
| US3947475A (en) | 5-Furoyl-2,2,4-trimethyl-1,4-dihydro-1H-1,5-benzodiazepine as an anti-inflammatory agent | |
| SE462972B (sv) | Nya bornanderivat, deras framstaellning och terapeutiska kompositioner innehaallande dem | |
| EP0052910B1 (en) | Derivative of n-acetilcysteine having therapeutical activity, process for its preparation and related pharmaceutical compositions | |
| DE1793336C3 (de) | D-Glucofuranoside, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate | |
| EP0211157B1 (de) | Isoxazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutischen Präparate | |
| US3457273A (en) | Derivative of phenylbutazone | |
| US20040023893A1 (en) | Novel coumarin derivatives and the salts thereof, a process for the preparation thereof and their use in the pharmaceutical field | |
| US4188482A (en) | Thiazino indole compounds | |
| DE69200900T2 (de) | 1,5-Diyn-3-cycloalkenderivate, ihr Herstellungsverfahren und diese enthaltende pharmazeutische Compositionen. | |
| CA1096860A (en) | Imidazole derivatives | |
| HU189556B (en) | Process for producing antranylic acid substituted with base and pharmaceutical compositons containing them as active agents | |
| EP0052909A1 (en) | Derivative of alfa-mercaptopropionilglicine having therapeutical activity, process for its preparation and related pharmaceutical compositions | |
| EP0280017A1 (de) | Neue Isoxazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate | |
| AT360043B (de) | Verfahren zur herstellung von neuen 9-substi- tuierten purinen und deren salzen | |
| DE3301959A1 (de) | 23-o-substituiertes carbamoyl-23-demycinosyldesmycosin | |
| EP0165017A2 (en) | Novel tetrahydro-B-carboline derivative and processes for preparation thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 8501884-4 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 8501884-4 Format of ref document f/p: F |